emivirine

CHEBI:44143 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pyrimidone that is uracil which is substituted at positions 1, 5 and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. A non-nucleoside inhibitor of HIV-1 reverse transcriptase, emivirine was an unsuccessful experimental agent for the treatment of HIV. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:38337 CHEBI:38337

Chemical structure

Computed structure properties
Molecular formula	C17H22N2O3
Charge	0
Average mass	302.374 Da
Monoisotopic mass	302.16304 Da
Source	ChEBI
InChIKey	MLILORUFDVLTSP-UHFFFAOYSA-N

SMILES

CCOCn1c(Cc2ccccc2)c(C(C)C)c(=O)nc1=O

InChI

InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

Also called

Coactinon (BRAND_NAME)— chebi
6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione (EXACT_SYNONYM)— chebi
1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione (EXACT_SYNONYM)— chebi
6-BENZYL-1-ETHOXYMETHYL-5-ISOPROPYL URACIL (EXACT_SYNONYM)— chebi
6-benzyl-1-(ethoxymethyl)-5-(1-methylethyl)uracil (EXACT_SYNONYM)— chebi
MKC-442 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:149950-60-7
kegg.drug:D01055
pdb-ccd:MKC
reaxys:7340168

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:36044 CHEBI:36044
CHEBI:53756 CHEBI:53756

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:44143`	emivirine	`antibioticmech:chebi-e98107dd91`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Gag-Pol polyprotein [588-1027]/[588-1147] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	40 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2849` `assay 429_1` `monomer 2337`	`PMID:11472208`
IC50	40 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2930` `assay 431_1` `monomer 2337`	`PMID:10052969`
IC50	40 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3042` `assay 440_1` `monomer 2337`	`PMID:14761194`

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585`	—	Human immunodeficiency virus 1	REVIEWED

PMID:11472208 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:10052969 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:14761194 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.